Chapter 12, Problem 12.28P

Interpretation Introduction

Interpretation: The reason corresponding to the fact that only one double bond of geraniol is epoxidized with the sharpless reagent is to be explained.

Concept introduction: Sharpless epoxidation involves the oxidation of double bond between carbon atoms to epoxide. This oxidation occurs only in allylic alcohol. This is an enantioselective oxidation, which means predominantly one enantiomer is formed. Sharpless reagents are $tert\text{-butyl}\text{hydroperoxide,}{\left({\text{CH}}_{\text{3}}\right)}_{\text{3}}\text{COOH}$; titanium $\left(\text{IV}\right)$ isopropoxide, $\text{Ti}{\left[\text{OCH}{\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\right]}_{\text{4}}$; and diethyl tartrate.